Fluorocompound having highly fluorinated norbornane structure, fluoropolymer, and their production processes

Abstract

To provide a novel polymerizable fluorocompound having a highly fluorinated norbornane structure, and a polymer obtained from the compound. Further, their production processes and a novel intermediate useful for the processes. A novel compound ( 1 ) such as a compound ( 11 ) or a compound ( 12 ), and its polymer. A compound ( 2 ) such as a compound ( 21 ) or ( 22 ), and a compound ( 3 ) such as a compound ( 31 ) or ( 32 M ), which are useful as an intermediate for the production of the compound ( 1 ), and its production process. However, each of Z A to Z E represents such as —CH(—OC(O)C(CH 3 )═CH 2 )— or —CF 2 , Each of W A and W B represents such as F, each of Y A to Y E represents such as —CH(—OH)— or —CF(CH 2 OH), and each of X A to X E represents such as —C(O)— or —CF 2 —.

What is claimed is: 
     
       1. A compound represented by the following formula (1): 
       
         
           
           
               
               
           
         
       
       wherein the symbols in the formula have the following meanings:
 Z A , Z B , Z C , Z D , and Z E : each of them is independently —CH(—OC(O)CT═CH 2 )—, —CF(—CH 2 OC(O)CT═CH 2 )— or —CR A R B —, provided that at least one of Z A  to Z E  is —CH(—OC(O)CT═CH 2 )— or —CF(—CH 2 OC(O)CT═CH 2 )—, and at least one of Z A  to Z E  is —CR A R B — (wherein each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom, T is a hydrogen atom, a fluorine atom, a C 1-3  alkyl group or a C 1-3  fluoroalkyl group); 
 W A  and W B : each of them is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; and 
 n: 0, 1 or 2. 
 
     
     
       2. A compound represented by the following formula (1A-1): 
       
         
           
           
               
               
           
         
         wherein the symbols in the formula have the following meanings: 
         Z: —CH(—OC(O)CT 1 ═CH 2 )— or —CF(—CH 2 OC(O)CT 1 ═CH 2 )— (wherein T 1  is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group); 
         W 1  and W 2 : each of them is independently a fluorine atom or a trifluoromethyl group; and 
         R 1 , R 2 , R 3  and R 4 : each of them is independently a fluorine atom or a C 1-16  perfluoroalkyl group. 
       
     
     
       3. A compound selected from either one of compounds represented by the following formulae: 
       
         
           
           
               
               
           
         
         wherein T 1  represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. 
       
     
     
       4. A process for producing a compound represented by the following formula (1), which comprises reacting a compound represented by the following formula (2) with a compound represented by CH 2 ═CTC(O)J: 
       
         
           
           
               
               
           
         
         wherein the symbols in the formulae have the following meanings: 
         Y A , Y B , Y C , Y D , and Y E : each of them is independently —CH(—OH)—, —CF(CH 2 OH)— or —CR A R B —, provided that at least one of Y A  to Y E  is —CH(—OH)— or —CF(CH 2 OH)—, and at least one of Y A  to Y E  is —CR A R B —; and 
         Z A , Z B , Z C , Z D , and Z E : each of them is independently —CH(—OC(O)CT═CH 2 )—, —CF(—CH 2 OC(O)CT═CH 2 )— or —CR A R B —, provided that at least one of Z A  to Z E  is —CH(—OC(O)CT═CH 2 )— or —CF(—CH 2 OC(O)CT═CH 2 )—, and at least one of Z A  to Z E  is —CR A R B —; wherein Y A  corresponds to Z A , Y B  to Z B , Y C  to Z C , Y D  to Z D  and Y E  to Z E , respectively; when each of Z A  to Z E  is —CH(—OC(O)CT═CH 2 )—, each of Y A  to Y E  is —CH(—OH)—; when each of Z A  to Z E  is —CF(—CH 2 OC(O)CT═CH 2 )—, each of Y A  to Y E  is —CF(CH 2 OH)—; and when each of Z A  to Z E  is —CR A R B —, each of Y A  to Y E  is —CR A R B —; each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; and T is a hydrogen atom, a fluorine atom, a C 1-3  alkyl group or a C 1-3  fluoroalkyl group; 
         W A  and W B : each of them is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; 
         J: a halogen atom; and 
         n: 0, 1 or 2. 
       
     
     
       5. A compound represented by the following formula (2): 
       
         
           
           
               
               
           
         
         wherein the symbols in the formula have the following meanings: 
         Y A , Y B , Y C , Y D , and Y E : each of them is independently —CH(—OH)—, —CF(CH 2 OH)— or —CR A R B —, provided that at least one of Y A  to Y E  is —CH(—OH)— or —CF(CH 2 OH)—, and at least one of Y A  to Y E  is —CR A R B — (wherein each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom); 
         W A  and W B : each of them is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; and 
         n: 0, 1 or 2. 
       
     
     
       6. A compound represented by the following formula (2A-1): 
       
         
           
           
               
               
           
         
         wherein the symbols in the formula have the following meanings: 
         Y: —CH(—OH)— or —CF(—CH 2 OH)—; 
         R 1 , R 2 , R 3  and R 4 : each of them is independently a fluorine atom or a C 1-16  perfluoroalkyl group; and 
         W 1  and W 2 : each of them is independently a fluorine atom or a trifluoromethyl group. 
       
     
     
       7. A compound selected from compounds represented by the following formulae: 
       
         
           
           
               
               
           
         
       
     
     
       8. A process for producing a compound represented by the following formula (2), which comprises subjecting a compound represented by the following formula (3) to a reduction reaction: 
       
         
           
           
               
               
           
         
         wherein the symbols in the formulae have the following meanings: 
         X A , X B , X C , X D  and X E : each of them is independently —C(O)—, —CF(C(O)G)- or —CR A R B —, provided that at least one of X A  to X E  is —C(O)— or —CF(—C(O)G)- , and at least one of X A  to X E  is —CR A R B —; 
         Y A , Y B , Y C , Y D , and Y E : each of them is independently —CH(—OH)—, —CF(CH 2 OH)— or —CR A R B —, provided that at least one of Y A  to Y E  is —CH(—OH)— or —CF(CH 2 OH)—, and at least one of Y A  to Y E  is —CR A R B —; wherein X A  corresponds to Y A , X B  to Y B , X C  to Y C , X D  to Y D  and X E  to Y E , respectively; when each of Y A  to Y E  is —CH(—OH)—, each of X A  to X D  is —C(O)—; when each of Y A  to Y E  is —CF(—CH 2 OH)—, each of X A  to X D  is —CF(—C(O)G)-; and when each of Y A  to Y E  is —CR A R B —, each of X A  to X D  is —CR A R B —; each of R A  and R B  is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; G is a halogen atom or a C 1-10  alkoxy group; 
         W A  and W B : each of them is independently a fluorine atom, a C 1-16  perfluoroalkyl group or a C 1-16  perfluoroalkyl group containing an etheric oxygen atom; and 
         n: 0, 1 or 2.